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Methyl formate

Methyl formate
Structural formula of methyl formate
Structural formula of methyl formate
Ball-and-stick model of the methyl formate molecule
Ball-and-stick model of the methyl formate molecule
Names
Preferred IUPAC name
Methyl formate
Systematic IUPAC name
Methyl methanoate
Other names
R-611
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.166 Edit this at Wikidata
EC Number
  • 209-282-1
UNII
  • InChI=1S/C2H4O2/c1-4-2-3/h2H,1H3 checkY
    Key: TZIHFWKZFHZASV-UHFFFAOYSA-N checkY
  • InChI=1/C2H4O2/c1-4-2-3/h2H,1H3
    Key: TZIHFWKZFHZASV-UHFFFAOYAI
  • O=COC
Properties
C2H4O2
Molar mass 60.052 g·mol−1
Appearance Colorless liquid
Odor pleasant[1]
Density 0.98 g/cm3
Melting point −100 °C (−148 °F; 173 K)
Boiling point 32 °C (90 °F; 305 K)
30% (20°C)[1]
Vapor pressure 634 hPa (476 mmHg) (20°C)[1]
-32.0·10−6 cm3/mol
Hazards
GHS labelling:[3]
GHS02: FlammableGHS07: Exclamation mark
Danger
H224, H302, H319, H332, H335
P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P312, P330, P337+P313, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
4
0
Flash point −19 °C; −2 °F; 254 K[1]
Explosive limits 4.5%-23%[1]
Lethal dose or concentration (LD, LC):
1622 mg/kg (oral, rabbit)[2]
50,000 ppm (guinea pig, 20 min)[2]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 100 ppm (250 mg/m3)[1]
REL (Recommended)
 TWA 100 ppm (250 mg/m3) ST 150 ppm (375 mg/m3)[1]
IDLH (Immediate danger)
 4500 ppm[1]
Safety data sheet (SDS) Oxford MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Methyl formate, also called methyl methanoate, is the methyl ester of formic acid. The simplest example of a carboxylate ester, it is a colorless liquid with an ethereal odour, high vapor pressure, and low surface tension. It is a precursor to many other compounds of commercial interest.[4]

Production

In the laboratory, methyl formate can be produced by the condensation reaction of methanol and formic acid, as follows:

HCOOH + CH3OH → HCOOCH3 + H2O

Industrial methyl formate, however, is usually produced by the combination of methanol and carbon monoxide (carbonylation) in the presence of a strong base, such as sodium methoxide:[4]

Base-catalyzed carbonylation of methanol with carbon monoxide to methyl formate
Base-catalyzed carbonylation of methanol with carbon monoxide to methyl formate

This process, practiced commercially by BASF among other companies gives 96% selectivity toward methyl formate. The catalyst for this process is sensitive to water, which can be present in the carbon monoxide feedstock, which is commonly derived from synthesis gas. Very dry carbon monoxide is, therefore, essential.[5]

Uses

Methyl formate is used primarily to manufacture formamide, dimethylformamide, and formic acid. These compounds are precursors or building blocks for many useful derivatives.

Because of its high vapor pressure, it is used for quick-drying finishes and as a blowing agent for some polyurethane foam applications (for example Ecomate® manufactured by Foam Supplies Inc.)[6] and as a replacement for CFCs, HCFCs, and HFCs. Methyl formate has near zero ozone depletion potential and zero global warming potential and a short atmospheric life of 3 days.[7]

It is also used as an insecticide.[citation needed]

A historical use of methyl formate, which sometimes brings it attention, was in refrigeration. Before the introduction of less-toxic refrigerants, methyl formate was used as an alternative to sulfur dioxide in domestic refrigerators, such as some models of the famous GE Monitor Top.

References

  1. ^ a b c d e f g h NIOSH Pocket Guide to Chemical Hazards. "#0417". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ a b "Methyl formate". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  3. ^ "Methyl formate". pubchem.ncbi.nlm.nih.gov. Archived from the original on 19 December 2021. Retrieved 19 December 2021.
  4. ^ a b Werner Reutemann and Heinz Kieczka "Formic Acid" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a12_013
  5. ^ W. Couteau, J. Ramioulle, US Patent US4216339
  6. ^ "Ecomate". Ecomate. Foam Supplies, Inc. Archived from the original on 2023-05-05. Retrieved 2023-06-14.
  7. ^ Wypych, George (2017). "2. Chemical Origin of Blowing Agents". Handbook of foaming and blowing agents. Toronto: ChemTec Publishing. pp. 3–28. doi:10.1016/B978-1-895198-99-7.50004-0. ISBN 9781895198997. ECOLOGICAL IMPACT Atmospheric life, days: 3 Kyoto compliant: yes Montreal compliant: yes Global warming potential: <1.5 Ozone depletion potential: 0
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